Formaldehyde → HCID 18770394, compound

HRID 1279430Notes

Reaction equation

HRID 1279430 reaction equation
[CH2:1]=O.[C:3]([BH3-])#[N:4].[Na+].N[CH:8]([CH2:23][CH:24]1[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH2:25]1)[CH2:9][CH:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]1.[OH-].[Na+]>C(#N)C.C(O)(=O)C>[C:19]([O:18][C:16]([N:13]1[CH2:14][CH2:15][CH:10]([CH2:9][CH:8]([N:4]([CH3:3])[CH3:1])[CH2:23][CH:24]2[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH2:25]2)[CH2:11][CH2:12]1)=[O:17])([CH3:22])([CH3:21])[CH3:20]

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 18770468HCID 18770468, compound

Product 1

HCID 18770394HCID 18770394, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolvent

Procedure

A 37% aqueous solution of formaldehyde (0.75 ml; 10 mmol) and sodium cyanoborohydride (194 mg; 3.0 mmol) were added to a solution in acetonitrile (15 ml) of 2-amino-1,3-bis(1-tert-butoxycarbonyl-4-piperidinyl)propane (373 mg; 0.88 mmol) synthesized by the above process, and the mixture was stirred at room temperature for 30 minutes. Acetic acid was then added to the solution to adjust the pH to about 5, and the mixture was stirred further for 30 minutes at room temperature. The reaction mixture was brought to pH about 10 by addition of aqueous 2.5N sodium hydroxide and extracted with chloroform. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resultant crude oil was purified by column chromatography on silica gel, thereby obtaining 388 mg (yield: 98%) of the title compound as a colorless oil.

Workup

  1. customsynthesized by the above process
  2. stirringthe mixture was stirred further for 30 minutes at room temperature
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resultant crude oil was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-388d900b638446ee8f003623e99fb1b3
Source dataset
uspto-grants-2002_09
Patent number
US06448242B1

Reaction notes

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